5284-29-7

Usage

Uses

Used in Chemical Production:
2-Dodecylphenol is used as an intermediate for the synthesis of antioxidants, which are essential in preventing the oxidation of materials in various industrial processes, thereby extending their shelf life and performance.
Used in Lubricant Industry:
2-Dodecylphenol is used as a lubricating oil additive to enhance the performance and longevity of lubricants. Its incorporation into lubricants helps improve their thermal stability and resistance to oxidation, making them suitable for high-temperature applications.
Used in Surfactant Production:
2-Dodecylphenol is utilized as a precursor in the manufacturing of surfactants, which are critical in reducing the surface tension of liquids, facilitating the formation of emulsions, and improving the solubility of various substances. Surfactants are widely used in detergents, cleaning agents, and personal care products.

Synthetic route

2-dodecyl(methoxymethoxy)benzene (130296-78-5) → 2-t-dodecyl-phenol (5284-29-7)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 16h; Inert atmosphere;	99%
With o-toluenesulfonic acid In methanol for 30h;	95%
With toluene-4-sulfonic acid In methanol for 30h; Heating;	95%

2-fluorophenol (367-12-4) + laurylmagnesium bromide (15890-72-9) → 2-t-dodecyl-phenol (5284-29-7)

Conditions	Yield
With 4-Fluorophenol; dichloro{1,2-bis[di(4-isopropylphenyl)phosphino]benzene}nickel (II) In diethyl ether at 0 - 20℃; Inert atmosphere; regioselective reaction;	79%

2-monochlorophenol (95-57-8) + laurylmagnesium bromide (15890-72-9) → 2-t-dodecyl-phenol (5284-29-7)

Conditions	Yield
With Ni(1,2-bis(diphenylphosphanyl)-benzene)Cl2; 4-chloro-phenol In diethyl ether at 0 - 20℃; Inert atmosphere; regioselective reaction;	69%

1-dodecylbromide (143-15-7) + methoxybenzene (100-66-3) → 2-t-dodecyl-phenol (5284-29-7)

Conditions	Yield
(i) nBuLi, Et2O, THF, hexane, (ii) /BRN= 506159/, (iii) BBr3, CH2Cl2; Multistep reaction;

1-<2-hydroxy-phenyl>-dodecanone-(1) → 2-t-dodecyl-phenol (5284-29-7)

Conditions	Yield
With hydrogenchloride; amalgamated zinc

O-methoxymethylphenol (824-91-9) → 2-t-dodecyl-phenol (5284-29-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) TMEDA, n-BuLi / 1.) THF, hexane, 0 deg C, 1.5 h, 2.) THF, hexane, a) 0 deg C, 1.5 h, b) RT, 12 h 2: 95 percent / TsOH*H2O / methanol / 30 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 1.) n-BuLi, TMEDA / 1.) THF, 0 deg C, 2.) 25 deg C, 12 h 2: 95 percent / toluenesulfonic acid / methanol / 30 h View Scheme

1-dodecylbromide (143-15-7) → 2-t-dodecyl-phenol (5284-29-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) TMEDA, n-BuLi / 1.) THF, hexane, 0 deg C, 1.5 h, 2.) THF, hexane, a) 0 deg C, 1.5 h, b) RT, 12 h 2: 95 percent / TsOH*H2O / methanol / 30 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 1.) n-BuLi, TMEDA / 1.) THF, 0 deg C, 2.) 25 deg C, 12 h 2: 95 percent / toluenesulfonic acid / methanol / 30 h View Scheme

1-dodecyl alcohol (112-53-8) + phenol (108-95-2) → 2-t-dodecyl-phenol (5284-29-7)

formaldehyd (50-00-0) + 2-t-dodecyl-phenol (5284-29-7) → C37H60O2

Conditions	Yield
In xylene at 175℃; for 10h;	85%

2-t-dodecyl-phenol (5284-29-7) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-2-dodecylphenyl dimethylcarbamothioate (29665-65-4)

Conditions	Yield
Stage #1: 2-t-dodecyl-phenol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: N,N-Dimethylthiocarbamoyl chloride In N,N-dimethyl-formamide at 80℃; for 7h;	82%

2-t-dodecyl-phenol (5284-29-7) + lead(IV) tetraacetate (546-67-8) → 6-dodecyl-6-acetoxy-2,4-cyclohexadienone (130296-68-3)

Conditions	Yield
In acetic acid at 25℃; for 10h;	76%

2-t-dodecyl-phenol (5284-29-7) + acetic acid (64-19-7) → 6-dodecyl-6-acetoxy-2,4-cyclohexadienone (130296-68-3)

Conditions	Yield
With lead(IV) acetate at 25℃; for 10h;	72%

formaldehyd (50-00-0) + 2-t-dodecyl-phenol (5284-29-7) → 3-dodecyl-2-hydroxybenzaldehyde

Conditions	Yield
With triethylamine; magnesium chloride In tetrahydrofuran for 16h; Inert atmosphere; Reflux;	69%

2-t-dodecyl-phenol (5284-29-7) + chloroacetic acid ethyl ester (105-39-5) → (2-dodecyl-phenoxy)-acetic acid (20803-58-1)

Conditions	Yield
With sodium ethanolate Erwaermen des Reaktionsprodukts mit wss. NaOH;

2-t-dodecyl-phenol (5284-29-7) + 3-monochloro-1,2-propanediol (96-24-2) → 3-(2-dodecyl-phenoxy)-propane-1,2-diol (97017-05-5)

Conditions	Yield
With sodium ethanolate

carbon dioxide (124-38-9) + 2-t-dodecyl-phenol (5284-29-7) → 3-Dodecyl-2-hydroxy-benzoesaeure, '3-Dodecyl-salicylsaeure' (30908-39-5)

Conditions	Yield
With potassium carbonate at 180℃;

2-t-dodecyl-phenol (5284-29-7) → methyl 6-oxo-4(E)-octadecenoate (130296-70-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 76 percent / acetic acid / 10 h / 25 °C 2: 70 percent / 4 h / Irradiation 3: 80 percent / Na2CO3 / methanol / 1 h / Heating View Scheme

2-t-dodecyl-phenol (5284-29-7) → methyl 6-acetoxyoctadeca-3(Z),5(E)-dienoate (130296-69-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation View Scheme
Multi-step reaction with 2 steps 1: 76 percent / acetic acid / 10 h / 25 °C 2: 70 percent / 4 h / Irradiation View Scheme

2-t-dodecyl-phenol (5284-29-7) → methyl (3R*,6R*)-6-dodecyl-3,6-dihydro-6-methoxy-1,2-dioxine-3-acetate (130296-77-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: 1.) O2, rose bengal (RB), 2.) TsOH*H2O / 1.) CH3OH, CH2Cl2, irradiarion, 1 h, 2.) 25 deg C, 40 h View Scheme
Multi-step reaction with 5 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: 1.) O2, CuSO4, 2.) TsOH*H2O / 1.) CH3OH, CH2Cl2, irradiarion, 12 h, 2.) 25 deg C, 30 h View Scheme
Multi-step reaction with 3 steps 1: 76 percent / acetic acid / 10 h / 25 °C 2: 70 percent / 4 h / Irradiation 3: 1.) O2, 2.) p-toluenesulfonic acid / 1.) rose bengal / 1.) CH2Cl2, MeOH, irradiation, 10 deg C, 8 h, 2.) 25 deg C, 40 h View Scheme

2-t-dodecyl-phenol (5284-29-7) → methyl (3R*,6S*)-6-dodecyl-3,6-dihydro-6-methoxy-1,2-dioxine-3-acetate (130296-76-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: 1.) O2, rose bengal (RB), 2.) TsOH*H2O / 1.) CH3OH, CH2Cl2, irradiarion, 1 h, 2.) 25 deg C, 40 h View Scheme
Multi-step reaction with 5 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: 1.) O2, CuSO4, 2.) TsOH*H2O / 1.) CH3OH, CH2Cl2, irradiarion, 12 h, 2.) 25 deg C, 30 h View Scheme
Multi-step reaction with 3 steps 1: 76 percent / acetic acid / 10 h / 25 °C 2: 70 percent / 4 h / Irradiation 3: 1.) O2, 2.) p-toluenesulfonic acid / 1.) rose bengal / 1.) CH2Cl2, MeOH, irradiation, 10 deg C, 8 h, 2.) 25 deg C, 40 h View Scheme

2-t-dodecyl-phenol (5284-29-7) → 6-oxo-4(E)-octadecenoic acid (138286-35-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: aq. NaOH / tetrahydrofuran / 1 h / 50 °C View Scheme

2-t-dodecyl-phenol (5284-29-7) → 6-oxo-4-hydroxyoctadecanoic acid (138286-36-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: aq. NaOH / tetrahydrofuran / 1 h / 50 °C View Scheme

2-t-dodecyl-phenol (5284-29-7) → 4-Methoxy-6-oxo-octadecanoic acid methyl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating View Scheme

2-t-dodecyl-phenol (5284-29-7) → 6-oxo-4-octadecanoic lactone (138286-38-1)

Conditions	Yield
Multi-step reaction with 6 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: aq. NaOH / tetrahydrofuran / 1 h / 50 °C 6: 90 percent / rose bengal lactone (RBL) / CH2Cl2; methanol / 6 h View Scheme
Multi-step reaction with 6 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: 1.) aq. NaOH, 2.) imidazole / 1.) THF, 50 deg C, 1 h, 2.) DMF, RT, 12 h 6: 32 percent / rose bengal lactone (RBL) / CH2Cl2; methanol / 12 h / Irradiation View Scheme

2-t-dodecyl-phenol (5284-29-7) → tert-butyldimethylsilyl 6-oxo-4(E)-octadecenoate (138286-37-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: 1.) aq. NaOH, 2.) imidazole / 1.) THF, 50 deg C, 1 h, 2.) DMF, RT, 12 h View Scheme

2-t-dodecyl-phenol (5284-29-7) → methyl 6-methoxy-3(Z),5-octadecadienoate (130296-79-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: TsOH*H2O / benzene / 3.5 h / Heating View Scheme

2-t-dodecyl-phenol (5284-29-7) → methyl 6-methoxy-3(E),5-octadecadienoate (130296-71-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: TsOH*H2O / benzene / 3.5 h / Heating View Scheme

2-t-dodecyl-phenol (5284-29-7) → (3R*,6R*)-6-dodecyl-3,6-dihydro-1,2-dioxine-3-acetic acid (138286-40-5)

Conditions	Yield
Multi-step reaction with 6 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: 1.) aq. NaOH, 2.) imidazole / 1.) THF, 50 deg C, 1 h, 2.) DMF, RT, 12 h 6: rose bengal lactone (RBL) / CH2Cl2; methanol / 12 h / Irradiation View Scheme

2-t-dodecyl-phenol (5284-29-7) → (3R*,6S*)-6-dodecyl-3,6-dihydro-1,2-dioxine-3-acetic acid (138286-39-2)

Conditions	Yield
Multi-step reaction with 6 steps 1: 72 percent / Pb(OAc)4 / 10 h / 25 °C 2: 70 percent / 3 h / Heating; Irradiation 3: Na2CO3 / 3 h / Heating 4: TsOH*H2O / benzene / 4 h / Heating 5: 1.) aq. NaOH, 2.) imidazole / 1.) THF, 50 deg C, 1 h, 2.) DMF, RT, 12 h 6: rose bengal lactone (RBL) / CH2Cl2; methanol / 12 h / Irradiation View Scheme

Upstream product

• 143-15-7 1-dodecylbromide 
• 100-66-3 methoxybenzene 
• 367-12-4 2-fluorophenol 
• 15890-72-9 laurylmagnesium bromide 
• 95-57-8 2-monochlorophenol 
• 112-53-8 1-dodecyl alcohol 
• 108-95-2 phenol 
• 824-91-9 O-methoxymethylphenol 
• 130296-78-5 2-dodecyl(methoxymethoxy)benzene 

Downstream Products

• 20803-58-1 (2-dodecyl-phenoxy)-acetic acid 
• 97017-05-5 3-(2-dodecyl-phenoxy)-propane-1,2-diol 
• 78576-60-0 C₃₇H₆₀O₂ 
• 130296-68-3 6-dodecyl-6-acetoxy-2,4-cyclohexadienone 
• 29665-65-4 O-2-dodecylphenyl dimethylcarbamothioate 
• 29688-04-8 S-2-dodecylphenyl dimethylcarbamothioate 
• 1296884-94-0 o-dodecyl-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamide 
• 1296885-05-6 o-dodecylbenzenesulfonyl chloride 
• 30908-39-5 3-Dodecyl-2-hydroxy-benzoesaeure, '3-Dodecyl-salicylsaeure' 

Relevant academic research and scientific papers

Salen-Based Amphiphiles: Directing Self-Assembly in Water by Metal Complexation

Tuning morphologies of self-assembled structures in water is a major challenge. Herein we present a salen-based amphiphile which, using complexation with distinct transition metal ions, allows to control effectively the self-assembly morphology in water, as observed by Cryo-TEM and confirmed by DLS measurements. Applying this strategy with various metal ions gives a broad spectrum of self-assembled structures starting from the same amphiphilic ligand (from cubic structures to vesicles and micelles). Thermogravimetric analysis and electric conductivity measurements reveal a key role for water coordination apparently being responsible for the distinct assembly behavior.

High ortho preference in Ni-catalyzed cross-coupling of halophenols with alkyl Grignard reagents

(Chemical Equation Presented) High preference of substitution at the position ortho to the hydroxy group was observed for Ni-catalyzed cross-coupling reactions of dihalophenols with alkyl Grignard reagents. Reactions of 2,4-dihalophenols, with various com

Overbased sulfurized alkaline earth metal phenates and process for preparing same

Overbased sulfurized alkaline earth metal phenates which are oil soluble, excellent in detergency dispersancy and have high base value, and an effective process for production of said overbased sulfurized alkaline earth metal phenates under conditions providing less sludge and less raw material recovery, and further a lubricating oil additives containing said overbased sulfurized alkaline earth metal phenates as a main ingredient and a lubricating oil composition which comprises said lubricating oil additive compounded in a lubricating oil are disclosed. Since the resulting overbased sulfurized alkaline earth metal phenates have high base value and excellent oil-solubility, they can be effectively utilized as lubricating oil additives.

Total synthesis of (±)-chondrillin, (±)-plakorin, and related peroxy ketals. development of a general route to 3,6-dihydro-1,2-dioxin-3-ols

Seven-step syntheses of the antitumor cyclic peroxy ketals la, 2a, chondrillin (Ib), and plakorin (2b) from (methoxymethoxy)benzene (8) have been achieved in 26-28% overall yields. The key step is the photooxygenation of enone 4 with a sun lamp using rose bengal lactone or CuSO4 as a sensitizer which gives a mixture of peroxy hemiketals 15 and 16 in 75-85% yields. Acetal formation in acidic methanol completes the syntheses of 1 and 2. The mechanism of photooxygenation was ascertained using 3-nonen-2-one (22) as a model for 4. Irradiation converts 22 to the cis-enone 23 which undergoes photoenolization to give 24. Dienol 24 undergoes a sensitized reaction with oxygen to give 29 and 30. The detailed mechanism of this last step is not known, although singlet oxygen is probably not involved. This reaction is general for any enone or enal which can undergo photoenolization to give a dienol. Peroxy hemiketals 33a, 41, and 43-46 were prepared in 30-80% yields. Peroxy ketals can be used for the synthesis of furans, diones, and pyridazines.

Process for treating 2-ethylhexyl p-methoxycinnamate in the presence of a phenol

A process for treating 2-ethylhexyl p-methoxycinnamic acid ester is described. The process comprises heating, preferably distilling, the ester in the presence of a phenol to insure that the ester is considered Ames negative.

Long-chain alkylphenols

A method for producing long chain-length alkylphenols with preferential production of para-alkylphenols and placement of the phenolic moiety at the #2 position on the alkyl chain. The reaction is carried out in the presence of crystalline zeolites having a major pore dimension of about six to seven angstrom units.